


High Stakes

by orphan_account



Category: Homestuck
Genre: Anal Sex, M/M, Masturbation
Language: English
Status: Completed
Published: 2012-09-23
Updated: 2012-09-23
Packaged: 2017-11-14 20:58:12
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,192
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/519439
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: <blockquote class="userstuff">
              <p>Dave has the strange, little, habit of sneaking into his bro’s bedroom at night… and masturbating over top of him.</p>
            </blockquote>





	High Stakes

**Author's Note:**

> It probably shouldn't need to be said by now, but I use bro and dirk interchangeably. There's some type of glitch inside my head that refuses to let me just use 'Bro' for everything. Whatevs, though. You're here for the porn anyway, right? And porn you shall have.

 

 

 

You promised yourself that you would stop. 

 

But somehow you still find yourself pushing open his bedroom door and creeping inside.  You watch him sleep, his chest rising and falling in a pattern that you’ve seen more times than you’d care to admit. 

 

When you first started doing this, you were unprepared and clumsy. You didn’t have the necessities to make things go as smoothly as possible. But that was weeks ago--seven of them to be exact--and now you know better. 

 

You spent ten dollars and seven cents on the softest motherfucking towel you could find. 

 

You stand at the foot of his bed, silently watching him sleep. His blinds are open and moonlight surrounds him, illuminating his skin, and makes you long to caress the light patch of blond hair just below his navel. 

 

A quick glance toward his bedroom door confirms that you’ve left it open. Good. You’ll need a clean get away in case things take a turn for the worse. 

 

Slowly and carefully as possible, you climb onto his bed. You try to balance the weight of your body to ensure minimal disturbance for him. You’ve done this enough where you know exactly where to position your hands and knees so that the mattress doesn’t make that alarming creaking sound. 

 

When you’re certain he’s not going to wake up, bolt upright, and punch the shit out of you, you push yourself to your knees. The towel is still draped over your shoulder, so you take it and place it on the bed in front of you. 

 

Okay, now you’re ready. 

 

Taking a deep breath, you slip your hand inside your boxers and free your cock, which is already hard in anticipation. As much as you want to close your eyes as you stroke it, you know allowing yourself the pleasure of getting lost in the sensation could lead to catastrophe. 

 

With one hand still wrapped around your dick, you lean down just enough to use your free hand to pull down his boxers, exposing his flaccid cock. You’re thankful that, like you, he doesn’t do the whole t-shit and lounge pants pajama deal like some people you know. 

 

You abandon your own cock for a moment to caress his to the point of hardness. You want to keep going, to pump his cock until he moans and shudders and spills his load all over you hand, but you’ve never gone any further than this. 

 

Long, slow strokes, gentle touches, so much fucking _longing_. There’s a constant burn in the pit of your stomach that directly correlates with how desperately you want to lean down and take his dick into your mouth. He’s big, big enough that you’d probably gag if you tried, but it would be more than worth it. 

 

Baby steps. 

 

You reluctantly release his cock to take hold of yours once more. You feel your eyes slipping shut so you force them back open again. Try as you might, you still haven’t perfected the art of masturbating to his hard dick while completely keeping your eyes open. 

 

You move quickly, your hand rapidly dragging back and forth, your toes curling each time your thumb swipes across the sensitive head. The pad of your fingertip glides across your slit, smearing a bead of pre-cum and making you hiss though clenched teeth. 

 

He shifts in his sleep and arches his hips, making his cock bob from the movement. 

 

You’re not sure what part of seeing this makes you cum, but you do, and _hard_.  

 

You practically shove your fist in your mouth to bite down on as your hips jerk forward of their own accord. Your eyes are open and you watch as squirt after motherfucking intense squirt spatters onto his cock. It falls from the tip and rolls along the shaft, settling at the base and generally creating a mess for you to clean with your trusty ten dollar towel. 

 

Feeling amazingly sated, you use this time to simply stare down at him. You wonder how soft his lips are, wonder if you kissed him, would he wake up and kiss back. 

 

_But you’re not insane enough to find out._

 

Pulling your gaze away from his face, you focus your attention on clean up detail. You lost control and made a royal fucking mess. 

 

The prince of fucking cumshot havoc. 

 

You tuck yourself back into your boxers and get to work with cleaning him as gently as possible. It takes longer than it should because you just really like touching him, but once you deem him clean enough, you quietly make your way off the bed and out of his room. 

 

You used to feel guilty the moment you stepped inside your own bedroom afterward, but you’ve managed to ignore those nagging thoughts altogether. 

 

As you crawl into your own bed, you glance at the clock. Even with how suddenly you came, it still took you six minutes longer than the last time you crept inside his bedroom. 

 

This is fucking cause for concern. 

 

The thrill of jerking your dick while hovering over your older bro is starting to dwindle and regardless of how stupid it is, you know you’ll keep pushing your boundaries until another thrill is ignited or until he catches you. 

 

You fucking hope against all hope that it’s _never_ the later. 

 

***

 

You’ve resorted to using your tablet for drawing nothing but stupid circles of various sizes. It’s late and you’re horny and you wish your stupid bro would just go the fuck to sleep so you can masturbate over his sleeping form like the fucked up twisted freak you are. 

 

You feel him loom over you and try not to shiver when his breath fans over across your ear. 

 

“Phenomenal improvement,” he says, taunting you. 

 

 _About as phenomenal as me jizzing all over you last night_ , you’d say, if you had lost your mind. 

 

“Bite me.”

 

He leans down and bites your shoulder in a matter that you’re certain was supposed to shock you and he succeeds. He also succeeds in instantly making your pants uncomfortably tight. Good thing your desk is made from quality wood. You’re pretty fucking positive your dick would drill a hole straight through it otherwise. 

 

He sticks his hand in your hair and fucks it up before walking toward the hallway. 

 

“Where are you going?” you ask. 

 

“Bed,” he answers. 

 

A few seconds later, his door shuts and you breathe a sigh of relief. 

 

_Finally._

 

You suffer through an hour of your cock going from hard to soft and back again while you give him some time to fall asleep. When you no longer hear any movement inside his bedroom, you grab your towel and proceed to further secure your position in Hell if you believed it existed. 

 

If you did, you’d have a penthouse suite on the top floor. 

 

You go through the routine of climbing on the bed, pulling out your cock, and pulling out your bro’s. Same thing, nearly every day, you’re a fucking master at this shit by now. 

 

It doesn’t take long at all to get him hard, in fact, you’re pretty certain this is the first time he’s ever gotten this hard, this _quickly_ out of all the other times you’ve done this. 

 

You’re ready to get this over with so you can go back to pretending that you’re not a sexual deviant, but you can’t stop staring at his lips. You’re tired of imagining what it would be like to kiss him and you think it’s stupid to avoid doing it because you’re too fucking cowardly, especially when you’ve spent the past five minutes fondling his dick. 

 

Fuck it. You’ve already got a ticket for an indefinite stay in the Hell you don’t believe in. Why not seal that shit with a fiery kiss of an incestual kind? You’re a high roller going all-in. 

 

You’re doing this shit, man.  

 

You brace your hands on either side of him and lean down. You hold back a groan when your cock glides against his. It wasn’t something you had planned, but you consider it an added bonus. 

 

You ignore the steady pounding of your heart when your lips are mere inches away from his. With a mixture of courage, stupidity, and crazy fucking _need_ , you press your lips against his. 

 

His lips are softer than you imagined. 

 

The kiss is _shorter_ than you imagined. 

 

It’s also _terrifying_. 

 

You feel his fingers grip your hair and wrench your head back. Your vocal chords are paralyzed from fear, so you don’t speak, but you _do_ go into panic mode and try to escape. His fingers grip at your hair and he easily uses years of natural talent to slam you against the bed. 

 

“Was it everything you’d thought it’d be?” he asks you, smirking down at the sheer horror on your face. 

You still can’t speak, so you just stare up at him, fucking eyes deer in headlights comically wide. 

 

“Dave,” he says your name with an authority about him that puts your fight or flight mode into overdrive. When you try to push him off of you, he forces you back down again with his hand pressed against the center of your chest. 

 

He presses himself flush against you. His lips latch onto your ear and slowly descend down your neck, kissing and biting the sensitive skin there until you have no choice but to cry out. You have no idea what to do with your hands, which first clinch and unclinch into fists, then grip at the sheets, and finally settle for wrapping around him. You dig your nails into his back when he grinds against you, his cock sliding against your own. 

 

He moves back and you whimper at the loss of the friction, but forget all about it when he slowly moves his way down your body, mouth catching your nipple and gently rolling it with his teeth until you can no longer stand it. 

 

“Ahh...fuck...”

 

“Sounds like a good idea to me,” he murmurs against your chest. 

 

You watch as he raises up long enough to lean over the side of the bed and digs in his nightstand. When he settles back fully on top of you, you pretend as if you don’t notice the bottle or its questionable slippery contents. 

 

“You’re getting on top, you little pervert,” he whispers and your natural reaction is to be turned on from the whole humiliation of it all. 

 

He watches you, one eyebrow quirked in amusement, while he makes you lube up his cock. 

 

Your legs are already trembling when you straddle him. Your fingers claw at the wall when he starts to push inside of you. You attempt to raise your hips, but he grabs onto them and slowly, inch by fucking deliciously painful inch, guides you down. 

 

When he’s fully inside of you, you slump forward because _fuck_ he’s bigger than you thought and you’re exhausted already. The sudden jerk of his hips, thrusting his cock deeper inside of you tell you that he’s nowhere near satisfied with this. 

 

“No sleeping on the job.”

 

Dirk Strider is a sadistic motherfucker who reminds you as he’s fucking you that he has a room full of puppets who are all here for a show. 

 

“Give them what they want,” he says after ordering you to jerk yourself off as you rock your hips, back and forth and up and down.

 

He won’t let you close your eyes. 

 

 _And it’s too fucking much_. 

 

He pulls your hands away from your cock, holding them with either of his own when you cum. You both watch as your dick pulses, ribbons of your cum squirting onto his chest and abs. Every fucking muscle in your entire body seems to go rigid and you can do nothing but shout out your release one amazing wave after another. Through your own cries of ecstasy, you hear him grunt and moan and feel when he grips your shoulders and slams upward, filling you, your contracting muscles greedily milking his cock.

 

Weak and unbelievably spent, you don’t have the energy to keep yourself upright when he jerks his hips again, causing you to fall over and slump on top of him. 

 

He kisses you, but you can’t keep up with it, so you just let him do whatever the fuck he wants. When he ends the kiss, he makes sure to use his teeth to tug at your bottom lip before resting his head back down against the pillow. He helps you roll off of him and onto your back. 

 

“I bet you enjoyed that, didn’t you, you little freak?” You don’t have to ask whether he’d been awake whenever crept into his bedroom. You’re pretty damn certain he was, each and every fucking time. “You and your little towel and your half-ass cleaning.” 

 

He confirms it anyway. 

 

“You’re demented,” is really all you can say, but you know that doesn’t fucking matter because so are you. Still, seven weeks of pretending to be asleep while your bro molests you is pretty fucking impressive. 

 

_House wins._


End file.
